Ep. 56-Alyssa Rapp: Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive

This is the You Winning Life Podcast, your number one source for mastering a positive existence. Each episode, we'll be interviewing exceptional people, giving you empowering insights and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, trainer and certified entrepreneur coach, Jason Wasser.

Everybody, welcome back. I'm with Alyssa Rapp. She's the founder of Bottlenotes, CEO of Surgical Solutions, lecturer at Stanford Business School, adjunct professor at the University of Chicago Business School, gubernatorial appointee to Illinois Housing Development Authority, and wife to the 2010 NLB World Championship player Hal Morris, mom to 2 children, but wait, there's more. In 2008, she was named to Inc. Magazine's 30 Under 30. Coolest entrepreneurs, and the wine industry's top 25 most influential people. And I'm just gonna stop there because there's a lot more to say about you, but thank you so much for having me.

And only correction is my husband won a World Series in 1990. I wish he'd won in 2010, but it was 1990. It was before my time. I couldn't see him play.

Got it. So I guess I just read that part, but congratulations. So first of all, congratulations.

Thank you. Thank you.

That's it, right? I, I'm always hesitant to introduce someone and say, and their spouse is also this, because universally known as to be a little cooler than I am.

So that's all good. It's all good.

Oh, well, we'll see. We'll see. So, um, because I know I'm very excited and I've been very excited to hang out with this time with you. So before we get into where you're hanging out now, and I know there's also a book that's recently come out, um, let's talk a little bit about how you ended up in this mindset of entrepreneurship before entrepreneurship became the cool thing.

That's a great question. So my I answer the question about how does one become an entrepreneur in a few different ways. First of all, I had great role modeling. My grandfather was an entrepreneur. He had fled the Netherlands during the Holocaust, and when he got back to Holland after with his— my grandmother and their then son, who did not make it through the war all the way, he was sad and had seen a lot of peril and was ready to leave those memories behind. So when he came to the US, he started by selling paintbrushes door-to-door. And he, over time, ended up figuring out with a consortia of other paintbrush sellers where the paintbrushes were made, and they figured out a way to buy the paintbrush factory. And they expanded that product line from paintbrushes to makeup brushes and later ended up selling the factory and the sales activity to the holding company, parent company for Crayola. And at that time, he also made a pretty strategic investment in a tech startup by modern-day language, which was called IBM. And so was able to retire and have his 70s and 80s to himself to travel the world again with his second wife, because my grandmother died sadly at age 50. And so we really— I learned from my opa that you can always start anew. I talk about this in the book, that anyone can become something in America. And so I had that imprinted into my my life and my life story before I even knew what that meant. And then my stepfather has been in my life for almost 30 years. He is an indomitable entrepreneur in Chicago, real estate developer and great civic activist, and also created something called the East Bank Club, still to this day the largest one-stop-shop fitness club in the country. So growing up and learning his walk-around style of management and seeing him in action, I couldn't help by osmosis but understand what it meant to start and run a business. And so I think that And again, those are two great Jewish elders in my life who were great role models. And I have many other role models and mentors who are both women and men, you know, even of different generations and younger generations than they. But I had great role modeling, so I don't want to discount that. I was born into a family where it was something that people did to start companies. That was door number one. Door number two is I had great— and the privilege of a great education. I went to Stanford Business School, and I knew I wanted to be an entrepreneur. I ended up falling into the wine industry, which we can talk about later. That was not what I set out to do by any stretch of the imagination. But I also was in a place like Stanford where in Palo Alto in the post-dot-com, the post-dot-bomb era of '03 to '05 as a student where nonetheless the ethos of the place is not why would you start a company but why wouldn't you. And I had tremendous education, incredible peers, awesome coaching, and great support. So again, I had great role modeling and then I chose a place and was fortunate enough to be accepted to a place where it was in the air. You start companies. And then thirdly, I fell in love with an idea. And I think that, uh, that, that process of falling in love with an idea, rightly or wrongly, is something that is necessary, albeit not sufficient, to being a successful entrepreneur. You can't— you gotta believe in what you're doing. And I think you actually kind of have to love it too, otherwise the shower time and the midnight, you know, wheels turning in your brain, it, it wouldn't be worth it. But all those three reasons are the why I think Jason Wasser ended up an entrepreneur the first go-round.

Well, the story that I'm hearing from you is so common. My family also— my grandfather escaped Nazi Germany in the Holocaust and came here to Scranton, Pennsylvania, opened up a furniture store years later, which is now third generation. My siblings have taken it over. And I became the odd person out going into the healing arts and now circling back around through entrepreneur and entrepreneurship coaching. And one of my beliefs is that entrepreneurship is one of the most incredible ways for self-actualization, self-potential. Because the focus from my perspective, and the people who know me and the people who have listened to these episodes before, are about the values-based decision-making. And I can't help anybody I work with, whether it's an individual, a couple, a family, a child, a teenager, or a business, if I don't know what your core values are.

That's really interesting that you should say that because I have had that conversation, I can't even tell you how many times in the last several days. Surgical Solutions, I took the helm, just over 2 years ago, and it was a classic reboot. It was a classic private equity-backed turnaround where there was a schism of performance, frankly, from what the private equity firm expected and they got. But what there really was was a schism of values. So I had to come back in and reboot and reset culture and reset the core values and double-click on the mission and really get alignment in the corporate team, which I have done and feel proud to have achieved. And now we have to take it to the next level throughout the organization and continue to make sure it trickles through. But I really do firmly believe that core values are, whether it's in your home life or in your corporate life, they should be what's driving decision-making. It gives me great pride as a parent to two delightful little girls who are 7 and almost 5 when I get the rewarding feedback from friends and teachers that they're so wonderful to have around, they're so well-mannered, they're this. They're not that way at home with me and Hal. But at least I know that the values and the coaching and the rubric through which we're raising them is at least imprinting on their psyche and is being translated externally, if not internally. And frankly, same holds true at a company. We started in the last year something called Leadership Lab for our mid-level managers in the company, and it's really a values-based decision-making leadership training, 4-module leadership training, because that's the kind of leadership coaching I got at Stanford Business School as a student and feel privileged to be a part of as a lecturer both there and at Booth. At University of Chicago, but at the end of the day, it's— I agree with you completely, Jason, that it's the core values that you hold as a team and as a company that should be driving the decision-making in the enterprise, in the field, on a day-to-day basis. I feel like that's not talked about enough.

Yeah, well, there's a lot of different aspects that you shared, and I have like all these different ideas running in my mind, where I heard a story of a buddy of mine who who left college in an entrepreneurship program because his brother went there. He said his brother loved the program and he was doing one of his projects with a professor and they had to do a business plan. And he went up to ask a question to the professor. And I think the question went along the lines of, when you made your business plan for your business, what did you do differently than what we were doing? Or what insights? And the professor responded like, oh, I've never owned a business before. And the next day he dropped out of school and he went into financial planning and has become really successful. And I wonder like, now it's 2020, you went to some really amazing schools, you were, we're around the same age bracket. And I'm thinking back to where I was in 2002, 2003 working for like nonprofits, specifically in the Jewish community. Where this idea of entrepreneurship, mentorship, leadership training was very, very, Leadership training was talked about. Culture wasn't talked about. And I know even today in 2020, cliché, it's very cliché to talk about company culture because it's like throw your core values up on your wall so when they see it when they walk in and when they walk out, as long as you have like, you know, a coffee Nespresso thing and free snacks and maybe someone coming in once a week to massage, you have a great company.

Yeah.

And I think that for me, I mean, first of all, I do believe in all those things. I believe that healthy snacks matter. I believe having great coffee and tea in the office matters. And I do try to bring in our friend Eric, the wellness executive, every 6 months. So I'll check the box on all those clichés, but I actually believe that culture is something that you have to walk the walk of on a much more frequent basis. So what's a better example? We do DoorDash Mondays because I want my people to have an extra spring in their step coming to the office on Mondays. They don't have to pack lunch. That's very— sometimes we do walk around management where we sit down and just chat about life during those lunch hours. We haven't done a lunch and learn in a while, and we probably should, but with someone from the outside. But either— even so, We, you know, that's one example. I believe in breaking bread matters. I try to have my team come out to a meal with me at my home or out and about with the executive team at least once a quarter, preferably once every 2 months. Breaking bread matters. Looking at people in the white of their eyes and having a meal and just having a conversation, some work, some non, but just being human beings breaking bread, I think is important for trust building and communication skills. I also think it's fun to do things that are non-core to the day-to-day operations together, like going to nonprofit events that are affinity core values and, you know, getting people to show up outside of the office and talk about how we work, we do in the world that is, is that other work being done in the world that matters, that complements our own. And, and so on and so forth. Recognizing birthdays, calling people when it's been a job well done, actually asking how people are doing through Slack as a technology tool that we've used to connect our entire 200-plus person field organization to the mothership. And that's a way where I can literally interact with anybody who works for us at any point in time, the stroke of a click. So I think that there are lots of things, but it is walking the walk. And then from a diversity standpoint, which I firmly believe in, not just because it's the right business strategy, because diverse opinions drive better decision-making, you know, I walk the walk. Just got to walk the walk, hire properly, hire well, hire diverse teams, take chances on people of all ages, shapes, and sizes who may not— who have high performance possibility and potential, but maybe not as much experience. All of that goes into, I think, how you can create a culture filled with promise and energy. And it's got to be very deliberate, and it's a day-to-day walking the walk piece of the puzzle. And I also believe you cannot ask people to work harder than you're working. It just is fundamentally uninspiring. And so, you know, to really be out there cranking is something that I think hopefully over time inspires people to say, "Well, my goodness, if she's out there working this hard, then she's not asking me to do something." she's not doing herself, well then I'll buy in. And that's not always the case, but in my life experience so far, that's been the fabric of a startup that I've maintained, I think, in all different phases of my career. That piece of it, mission-driven, we're all sprinting toward the same finish line in a 2 to 3 year timeframe, that psyche is certainly what I think characterizes my approach to business, rightly or wrongly. It's probably not right for everyone and right for every situation, but in the ones I've chosen or that have chosen me, it seems to be the right Objectives are a huge part of it, right?

Setting timeframe-based goals, breaking it down, action tasks versus we're just trying to hit a number.

It's got to be measures, dimensions of accountability, by when, by whom, for what end, and measure. And my acting COO, a veteran business leader, Tracy Wan, who had been the president and CEO of the Sharper Image and then of a PE-backed company called Cycle Gear, and now with us, she has this great line that what is inspected is respected. And that's including goals. I mean, we were just having our 2020 goals conversation this morning. It's just got— they gotta be on paper and they gotta be discussed and communicated and wrestled with, and then they gotta be put on the wall next to the desk or put on the virtual wall and reflected upon. That matters.

Well, accountability, right, is a huge part of that process. And I'm hearing you talk, I'm so much of what you're saying, because the platform in which I created this for, right, as a therapist who focuses on mind-body integrative health, and then has come around the last 3 years with, according to my coach, Rick Sapio, who's a capital venture investor in Dallas. I'm not sure if you're familiar with him, but he has a great program called Business Finishing School. Awesome. That's how I got shifted from the idea of being like a healer therapist to like, Oh my gosh, I'm an entrepreneur. And my role right now happens to be serving in that way, and that whole servant leadership through Howard Behar from Stanford.

That I believe in firmly.

So, and Rand Steigen, all these. So I've been introduced to all these people through this wonderful network with this mindset of I'm just a therapist in South Florida in this corner office. And, you know, I get to use this platform to hang out with people like you and other people to merge and meld ideas. But everything you've been saying also sounds so incredibly applicable to a family, to a teen, right? I can break down with you, and I'm sure you could as well, every developmental stage of a person's life and apply everything.

Well, I'm sure you would do better than I, but what I can tell you that I've learned in business, and I certainly believe applies with families and children and spouses and family members, is showing up matters. Showing up matters. Doing what you say you're gonna do Matters every single time. And, you know, I hold myself to that level of accountability. And so then it's— I try to hold my children to it. I am not a perfect parent. I understand there is no such thing. On the other hand, I also try to observe patterns, whether it's people I manage or people with whom I live. And I've noticed that with my children, and we noticed this a couple of years ago, that if they got screen time, even if it was an educational game like Osmo on the iPad, before school they turn into monsters. It was like the mind meld was happening, they turn into monsters. So we just decided there was going to be a no screen before school rule. And now we try to have a no screen rule Monday through Thursday as a whole, unless someone's traveling and, you know, it's desperate times, desperate measures. And if there is, if we break the rule, we're very clear that it's time-bound. I'm very clear. It's a 12-minute, here's the timer. And if there's any drama when it goes off, there will not be this, you know, we will not have this cheat tomorrow. And I think that It's this whole notion of self-regulation with children, of course, but expectation management, at least with our kids, is helpful. It's hard, but really, really helpful. You know, the alligator tears fly when you got to catch a 6 AM flight and they hear you leaving at 4 and they come out, you know, wanting to hang on to your ankles.

And I don't—

well, leaving at that point, obviously it's pretty heart-wrenching. On the other hand, tell them the truth. Mommy's got to go for 36 hours. Mommy will be back tomorrow night. Or if it's, you know, I will see you and here's what's happening in the 36 hours I'm gone. Here are the extra special fun things that will happen while I'm gone. I'll see you. And it's not easy, but at least it's honest and direct, and here's what the expectations are. And then you follow through and do you say what you're going to do. And with people at the office, particularly when you talk about this notion of managing through values and expectations, it's— I find in my experience in business, maybe probably different from my experience as a parent, is that I try to lead with a very— I try to lead professionally with a very long leash. Aka, I'm going to be very clear with you what my expectations are, and I'm going to let you go figure it out. Good luck swimming in the deep end. And if you need me and you need more support, please come find me, and then I'm happy to provide it. But I'm going to assume you are capable of getting it done and you don't need me to micromanage the outcome. And by and large, not always, I have been burned a couple times by that approach, but 9 to 9 times out of 10, that's been a productive approach for me. And I end up getting the best out of people because they say, oh my God, She believes I can do this and I've never done anything like this before. Well, Jesus, I better work nights and weekends to figure out how to do this. And I'll come with questions and advice. I'm not going to start drowning and not ask for help. But I have found that to be a productive way to manage, whereas with my children, I would not throw them in the deep end, but, you know, without being able to swim, although thank God they can swim. But, you know, that— there are a lot of parallels. There's no question about it. Definitely.

Yeah. And I'm thinking of all these, like, the thousands of conversations I've had over the last 2, 3 years with other entrepreneurs and other people in the business world, and this theme is running, right? If you put your expectations up front, here's what you can expect, here's what you shouldn't expect, here's what's gonna happen. I literally had this with a coaching client the other day, and I'm like, what would happen if you started, and he's in commercial assessment, appraisals, and I'm like, well, what would happen if they come in and you say, what's the number you think you're getting from this appraisal? 'Cause they might say like it's a $10 million thing and they're really only gonna get 6. And then when they get the number of 6 or 5, they're like really pissed off at him, right? So I said like, start asking them what do they actually think walking in.

I think that the negotiation strategy of, and so there's obviously two schools of thought. I've never put the number out first because you don't have your living value on the table. Then there's the other point of view, which is this is best and final, I'm not playing games. And you obviously have to mean it. Just like if you say, if you hit your sister again, you're going to timeout, and have to follow up. But I used that strategy very recently with a couple trickier scenarios, which was, listen, I made you offer for X, was it X? You came back and asked for 3X, and I said, no, no, it's actually X, best and final, or X plus 0.5, and that's best and final, and then we're walking. And I meant it and was prepared to. And two different strategies, one with someone exiting the company and one with a major customer that we were renegotiating pricing, I actually meant it. I'd gotten to the point where they were asking us to do things that were unsustainable for the business. And I said, it's best and final, take it or leave it. If you leave it, I'll be devastated, and that's life. And they took it, and now we're done. So my point is, is that I think that that notion of end-running some of the charade, I don't have a lot of patience for it, to be honest with you, but end-running this charade is something that I firmly believe is beneficial to negotiation. And it is counter to lots of negotiation strategy of the zone of compromise and anchoring and start with something that you know, you know, never the first time or not. And I've taken those courses, I have learned from those wise people, and I agree with that strategy in some select cases. And then there are cases where there's downside risk, like your client, where if they piss off the customer, then that person might walk and they might not get anything. So better to expectation manage up front and just say, listen, this is not— exactly.

And in this situation, he's not even doing an assessment. This is before they've even done an assessment on the property. The client coming in saying, here's what I think it's worth. My client has no clue and it may be worth more, it may be worth less, but I'm challenging him to say, I just wanna let you know, just because you think it's worth it because it's 10 blocks away from another property that's worth that money doesn't mean it's zoned or whatever.

It's the same thing I say to my friends who are in their 40s dating. I'm not gonna lie. I mean, one of our very close guy friends, Hal and I have a very close friend who's a terrific person, we both think he's great and should be a great fit for someone. But he's like 48, never been married. There was some family tragedy 10 years ago which caused a little bit of a time— I call it a time gap because it diverted his focus to his brother, his late brother's family, etc. But he's like this great guy alone in California running a family business, doing really well. And I have two comments to him. One, no one's coming down the chimney. Santa doesn't exist. For dating. I'm not going to burst the bubble of any children that might come across this podcast. Two, um, I mean, two, don't keep making the same mistake you've made for 20 years. Like, if you haven't met the right girl at the bar the last 20 years and you're a Dartmouth undergrad with a Berkeley law degree, probably not going to meet the right girl at the bar in year 21. And door number 3, cut your losses sooner if you are seeing warning signs. People show you who they are in a relationship real early, real clearly. I've seen it in business. And it's hard to pay attention, but it's, you know, shame on you if you don't, especially as you get older and wiser. So, tigers don't change their stripes, at least not very quickly.

Right, and we tend to make the same mistake not 5 or 6 times, but 20, 30, 40 times in a row before we change that pattern. So let's go back, 'cause I know our time is limited, but I wanna go back to Wine Notes and how that happened and how you ended up there. And then taking it a little bit more into the context of your personal experience of female entrepreneurship and what's going on in that world.

So Bottle Notes was something I started while at business school, and it was an idea that came out of a whole amalgamation of different courses and studies and an internship and things. There's a great chapter on it in the book Leadership and Life Hacks, which you can get on Amazon. And the problem I identified in the marketplace was that The internet was being insufficiently utilized to match people to products in the '03 to '05 era. And what better product is one as opaque and complex as wine? And the next generation wine consumer was also on the rise demographically and buying more wine at higher average price points and higher average quantities than the boomers. Now that's shifted in the last year. So now we're 15, 16 years later, that's shifted and the share of buzz is being absorbed by craft beer and canned, canned spirits and hard seltzers and all those other things and cannabis products, etc. So it's a much different world. But then rolling back 15, 16 years, it was amazing to say, it was that millennial consumers were drinking more wine at our higher average price points and higher average quantities than the boomers and were not feeling connected to by the wine enthusiasts or Food Wine or all these sort of baby boomer friendly, highbrow, low approachability platform. So we were trying to blow the lid off the industry, be the wine enthusiast or Food Wine for the next generation. We started as the Netflix for wine as an e-commerce play. Great chapter in the book, probably one of the best and strongest on pivoting versus quitting, where we had to pivot our strategy from e-commerce to media because of a big regulatory shift. But that was a very organic change where we could have put up the white flag or pivoted. It was a hard, hard, hard, hard thing to do, particularly in '08, given the financial crisis, but we got it done. And so really, that was a very explicit lesson in stick-to-itiveness, grit, a dogged entrepreneurial spirit, all the things you hear about in the journey of an entrepreneur. But for us, we were also really, really focused on the customer. We were always focused on solving a problem for the customer, which was initially getting them wine tailored to their personal taste using patent-pending matching technology, and over time as we pivoted strategies, helping educate and entertain them about wine in ways in which they wanted to be educated and entertained. Email newsletters, large-scale interactive events, we toyed with an app, I wrote my first book, Around the World in 80 Sips, Name That Tune. We were educating and entertaining the next gen, and then brands, wine, And non-wine luxury brands were advertising through us to reach our audience. So that focus on what does the customer want and giving them what they want, when they want it, how they want it is, I mean, that transcends industry and that was one thing we did really well.

That's interesting, so I'm thinking like there's like breadth of like you focus on a niche and you chunk it down, you chunk it down, I always talk about this and some of my mentors have like, you know, what is like that, at the end of the day, what's the niche in the niche in the niche?

The richness are in the niches. Exactly, right?

And the crumbs left on the table in a major industry if you just solve that one problem.

Well, especially if you're focused. Right? Excuse me. What I found the hard way is that what's hard to do is figure out what not to do as much as what to do. Yeah.

Right, an entrepreneurial ADD is one of the things I call it.

It's really hard. It's really hard not to chase the new shiny toy. Though that was a mistake I made the first time. I was focused when we pivoted, but I wasn't willing to let go of one or two legacy products. I couldn't let go and they were great ideas and they could have been businesses of their own. But I don't know if I'd go as far as to call it entrepreneurial ADD, but entrepreneurial unwillingness to let go. That was hard and it's very real and I've gotten much more disciplined and I'm also much more disciplined now in that I have made some angel investments. Every time I've made one, I literally, I mean, when I tell you I literally write it off in my mind, I don't even think about it. I'll do anything for the entrepreneur. I wanna be helpful. The second I've written that angel investment check, pretend like it went up in flames because no matter how good the idea, how smart the entrepreneur, it's a 9 out of 10 it won't work and I'd be happy to help and hope it'd be the 1 out of 10, but I don't think about it. Whereas, so I do that with a very small piece of my personal portfolio because that's not a strategy, good investment strategy to write checks and light them on fire. Alternatively, with seed stage investing and venture, I've tried to take a more pooled approach where my family and I have a couple— collective investments in seed stage funds where I have really smart people whom I love and trust canvassing the strat— the land for their particular strategy and niche around seed stage investing. And while my upside will be capped because we're part of a consortium and a fund, my downside risk should be a little bit lower because professionals are looking and vetting, etc. Um, and that's been a way to sort of stay involved without lighting checks on fire. As often, but it's the thing I look at when I look at anything personally and directly or indirectly through these funds as they come through is that narrowness of purpose and focus. Because that focus, that clarity of purpose, you can't control for industry dynamics all the time. You can pick a big enough industry as we discussed, but there are things you can't control. Coronavirus, et cetera, et cetera. But what you can control is how focused you are on your strategy. And that, the more focused, the better in my mind. Exactly.

Ah, yeah. There's so much good stuff there and I have like 14 different things that I wanna ask and share with you. But you were talking about, you know, the numbers and being laser-focused. As a female entrepreneur, when the numbers are finally growing, finally shifting and changing, the landscape's changing and before, we're having a pre-conversation about billions and the female billionaire entrepreneur this season. What's that journey been like specifically for you? Right, you already came from this background, you were already supported, you already went to a good school. Where are some of the challenges?

Well, listen, I mean, I was trying to make waves in a male-dominated industry, in a male-dominated— two male-dominated industries, tech and wine. And I was doing it pre-MeToo. So every MeToo story you've heard, I lived. It was awful. I lived it all. It was ridiculous and demoralizing and absurd, and it inspired me to pull together great women venture capitalists from Silicon Valley who are close friends and put panels on at Stanford Business School on what it's like to be a woman in venture capital. Cut to present, it has inspired me to teach a new class at the University of Chicago Booth Business School on women as CEOs, investors, directors, and board members. Like, that's coming up next month. Like, I'm walking the walk. But in between those things, you know, these seed stage investment funds I mentioned to you, the strategies for one of them, Lead Out Capital, is invest in women and diverse CEOs. Impact Engine, Double Bottom Line, impact through the activities of the firm, plus diverse leadership teams. Corazon Capital, founded by a dear friend of mine, Sam Yagan, they do seed stage investing, but he's got an extraordinary track record on diversity. So, and there are others. Another classmate started something called Jane VC I'm really excited about. Directly invest in female entrepreneurs myself. So I think that the numbers have improved. MeToo is MeToo. There's a lot lower tolerance. There's a lot more scrutiny, and there's a lot more investment by women in women and by diverse, you know, investors in diverse leadership. And yet I think about my own career, and I think about my own career in private equity, and I think about my own aspiration to be on a public company board someday, you know, hopefully not 20 years from now, more like 5 or 10. Only 7% of those public company directorships roll over every year. 7%. So it doesn't matter if you've got the perfect resume or the great network, and you need all those things, are necessary, not sufficient. You need the openings. And so I think there are pluses and minuses to regulatory strategies that mandate diversity. I really do. I just love for companies to do it because it's the right thing to do, and I think Goldman Sachs recently set a pretty great precedent on that. So I'm not saying I think it has to be regulated. In fact, I prefer for people just to do it because it's the right, good business practice to bring diverse viewpoints to the leadership table, board table, executive team, etc. But, you know, I lived in an era where, I mean, the stories I could tell you would, you know, knock your socks off. And I think that I'm grateful that I got through it relatively unscathed. I lived some of that stuff the hard way. I was super lucky and feel very blessed that I was with my husband through that whole era. We weren't married till, you know, a piece of that time, but he's— he lived that movie with me and he had my back and he, you know, I was sounding board. And I think that having a great partner, irrespective of gender, is an incredibly important thing to have in entrepreneurship. I think it's a lonely road. Um, and I feel very lucky that I— Hal was my person throughout the whole thing. I, I don't— I'm not— I don't know if I wouldn't have made it, but it wouldn't have been half as fun. And it's not to say it was all rainbows and butterflies for him or us in that phase. It's a hard thing to do. It is a hard thing to do, whether you're Mark Zuckerberg or me, it's a hard thing to do. People underestimate because of fantasies and shows like Billions, which I like, you love, and because of the biases in the popular press, we focus on the unicorn outcome, but you don't focus on what it takes to get there. It is hard. It is hard. Some have it easier than others, but it's hard. I think that that's the piece that's undersung. And it's that much harder if, you know, you're Ginger Rogers doing it backwards in heels. I mean, that's just the reality.

Right. And then you have you, you have a Sarah Blakely, you have all these different, right, who are changing the space, going on in the experience of what's going on. And because I love, um, I did a program, Build Your Life Resume, with Jesse Itzler, which is one of his online communities, and they're very much welcomed, like the community is very much welcomed into their their home life because they show like, this is how we do our life balance. This is how we parent. This is how— so I'm really curious for you where you married a professional athlete where you're incredibly driven. I'm assuming he's as incredibly driven to become an elite athlete at that level. How important is that in relationship dynamics from your experience? I know you can't speak for Mary, but in your— how much of that was something that you were looking for And what have been some of those pros and cons of having two people who have been elite?

You know, I think I chose someone who was an athlete because I was at a different sport in a different time in a different era and league. But I was a very serious gymnast and dancer from 7 to 17, like, well, 21 through dance, 3 hours a day, 6 days a week. So the irony is I keep the joke that I probably cranked harder and more dedicatedly growing up than he did, although he obviously is an extraordinary talent. Deeply admire his talent and his drive and his dedication. So that— those are all pieces of what I knowingly and unknowingly chose. I definitely think that being an athlete is core to who I am, it's part of who he is, and those are big pieces of it. Being on a team matters to both of us, and I view us as a team. We absolutely unequivocally are different. I'm an extrovert, he's an introvert, blah blah blah blah blah. So the opposites attract piece, and then there's the also piece of it where We have very, very, very complementary values. There are very few times that our values are out of step on anything ever. And that is also pretty core because it means that, okay, he's the introvert, I'm the extrovert, we're gonna squabble about how many social outings we have in a given month, that is a squabble. How often do you have to drag him out? But what we're never gonna squabble about is what to invest in, how to spend our money, how to family first, we're not, I mean, none of that stuff. We are just in lockstep on all of it. Well, yeah, I think so. I mean, I do think so. And so I think that the grit and the ability to keep swinging, I dedicate the last chapter of the book, my book Leadership and Life Hacks to him. And he has reminded me in those entrepreneurial years and present, until the ninth inning and the third out, you have to keep swinging because you never know how the tide may turn. And that I learned myself on my own prior to our relationship, but it has been wonderfully reinforced. Forced through it. And I think that, you know, so the values and the kindred spirits and souls, I think, is really matter— matters. You know, we're very, very, very different people. We're also good Midwesterners who really fundamentally above all else value hard work. And, and that I think is also pretty important. I think people have many different types of marriages that work, and as far be it for me to comment on anyone else's— we all know the politics of people's personal lives are are A, personal, and B, complicated. But I do know that the old adage of pick someone, you know, with whom you can never run out of things to discuss, where there's enough overlap to have shared interests, but enough— the Venn diagram has enough lacking in overlap enough so that there's always— I always feel like I could learn something from him, and I hope and think he probably feels the same way. Because otherwise, you know, life is long, and, you know, at the end of the day, you gotta still connect. And I think with kids, You know, my husband was married once before he had— before we met, and he has children from his first marriage, and his eldest child is someone with whom I have a great relationship. And that's also been its own journey, and he was also very, very open to me having my own relationship with his eldest and grateful for the input and role I have had. And that helped, right? That helped to make it all work, because I have a stepfather with whom I have a wonderful relationship. He's been extraordinary to me. And so I was hopeful that I would be able to provide that role in some way, shape, or form to any of his children. But it's— life is complicated. Postmodern family life is complicated. It ain't easy being green. You just got to keep on keeping on. And, um, and you know, two little girls, as precocious and delightful as they can be, are a lot of work juggling with the work and the marriage and the civic activity and the teaching and the rest in the book. And, um, and so it's, you know, I don't— I guess a good closing comment will be one thing I get asked about the book a lot is, what's your favorite hack? Since it's Leadership and Life Hacks: 100 Tips for Living Your Life More Efficiently with Greater Impact. And I think the best hack I've got that encompasses both business and family life is episodic versus daily balance. I cannot, I do not try to get everything done in a given day because it would be a colossal failure. And like this week, Hal's at spring training, which is fantastic for business, which is fantastic because I don't have to, he's not, I miss him, but it's easier to balance when I'm not also trying to satisfy that stakeholder, right?

So this week is about being a mom and a CEO.

Like that's this week. I'm doing a little bit of PR around the book. Like that's this week. And I try to nail 2 stakeholders a day and do something for 45 to 60 minutes every day for myself. And that's how I try to, you know, put your own oxygen mask on first, take care of you so you can take care of others. And then obviously really show up and be present for my kids and my career this week. And then there'll be the set, and then the episodic balance. Case in point, Al has a colleague getting married and he really wanted me to go for 24 hours. So we're gonna punch out and go to Boston, do a Boston run for 18 hours Saturday to Sunday. That'll be time I'm not CEOing and not momming, but I'm gonna like show up and be a great wife. And so it's, so over the course of 7 or 10 or 14 days, I hope to achieve all, be everything I need and want to be to each of those stakeholders, but it's not getting done in a single day.

So then before I let you go, the last question really related to that is what's one self-care activity that you think you, that you maybe have experienced or seen other entrepreneurs lacking?

I see, and I see this entrepreneurs and non, I see my friends who are in very, very busy work phases of life, married or not, kids or not, not doing that 45 minutes a day for themselves. Like, one of my best friends in the world is a superstar surgeon. She's fantastic. And there was a period of her life where she just was not giving herself her 45 minutes a day. I mean, and for me, that's working out. For her, it could have been meditating or, you know, extra sleep. I mean, I'm not here to tell you what your one thing is, but she was just getting depleted. And I said, listen, the irony is you need to take the time for yourself to put your own oxygen mask on first. And, you know, for her, it ended up being working out too. It wasn't even how you look, it's how you feel, and you got to take care of you. And so I think that letting it go— and I'm not saying it's easy. I hate 6 AM flights, you know, they kill your— you have to get up at 3:30 in the morning to get the workout in, which I do sometimes and not others. Like, that's hard. But at the same time, you know, don't let perfection be the death of progress. Just take care of yourself a little bit, even if it's a 10-minute meditation, not the 45-minute workout, God forbid. Just do something. To take care of you because the clock keeps turning. Time keeps, you don't get the time back. So, you know, I think that's the take care of you. It's easy to get lost in the dream and in the grind. It's easy because I remember, you know, my first startup, you know, you turn on your computer, you know, Hal and I were living together but we didn't have kids yet. Turn on at 6 AM and then you get sucked in and before you start your day you're running pants and it's 11 AM, don't get a bite to eat. 2 people you're virtually in your gig economy working on it with, they're taking a break, and you're like, okay, well, I'm gonna take a break, I'm gonna work on that, bye, and the email keeps going and the phone keeps going, the Slack keeps going, and it's easy to not do it, and you just have to carve out the time.

Right, it's like the text fast or a Sabbath or whatever, right, space that different communities have that's created are so important. Again, that's also scheduling it in, rhythming and ritualizing.

Totally, I schedule everything, and that's, I think the ritualing it in is your phrase, it's really a really good one. That's the— that's what's got to happen, Jason. It's got to be ritual then. It's not something that's movable, just like a call with your executive team wouldn't be movable. It has to happen. This is when it happens. It happens. We schedule around it. It's a non-negotiable. It's a non-negotiable. It's a sacred time, like you have to take a shower. You have to have your 45 minutes.

Awesome. Thank you so much for coming on.

Thank you for having me. I'm flattered to have had you, and I applaud all the great work you're doing coaching people. They're lucky to have you.

Thank you.

Thank you.

And everybody, please, please, please check out the book. Amazon was right, the main place you can get it, right? It's Leadership and Life Hacks.

Yeah.

And check it out.

Yep. AlyssaRapp.com. All the above.

Awesome.

Awesome. Thanks so much for having me.

Thank you so much.

Bye.

Thanks for listening to the You Winning Life podcast. If you are ready to minimize your personal and professional struggles and maximize your potential, potential, we would love it if you subscribed so you don't miss an episode. You can follow us on Instagram and Facebook at Jason Wasser LMFT 🎗️.